(3S,4R,6R)-(4-hydroxy-6-(6-tert-butyldiphenylsiloxy)hexyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

Base Information

Chemical Name:(3S,4R,6R)-(4-hydroxy-6-(6-tert-butyldiphenylsiloxy)hexyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester
CAS No.:303007-77-4
Molecular Formula:C₃₄H₅₁NO₆Si
Molecular Weight:597.868
Hs Code.:

Synonyms:(3S,4R,6R)-(4-hydroxy-6-(6-tert-butyldiphenylsiloxy)hexyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

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Chemical Property of (3S,4R,6R)-(4-hydroxy-6-(6-tert-butyldiphenylsiloxy)hexyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

Chemical Property:

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Technology Process of (3S,4R,6R)-(4-hydroxy-6-(6-tert-butyldiphenylsiloxy)hexyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

There total 10 articles about (3S,4R,6R)-(4-hydroxy-6-(6-tert-butyldiphenylsiloxy)hexyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 303007-71-8
(3S,4R,6R)-(-)-4-hydroxy-6-(6-hydroxyhexyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester

: 303007-77-4
(3S,4R,6R)-(4-hydroxy-6-(6-tert-butyldiphenylsiloxy)hexyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1021/jo000447q

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 303007-77-4
(3S,4R,6R)-(4-hydroxy-6-(6-tert-butyldiphenylsiloxy)hexyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 63 percent / NaHCO₃ / dioxane / 5 h / 30 °C

2: Na / benzene; methanol / 48 h / 20 °C

3: triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

4: H₂ / Pd/C / ethyl acetate / 24 h / 50 °C / 22801.5 Torr

5: H₂ / Raney-Ni / ethyl acetate; H₂O / 24 h / 80 °C / 60804.1 Torr

6: 3.9 g / TsOH / methanol / 1 h / 20 °C

7: 85 percent / triethylamine; DMAP / CH₂Cl₂ / 6 h / 20 °C

With dmap; hydrogen; sodium; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; nickel; In 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; benzene; 1: Acylation / 2: Dieckman condensation / 3: Substitution / 4: Catalytic hydrogenation / 5: Catalytic hydrogenation / 6: Hydrolysis / 7: Substitution;
DOI:10.1021/jo000447q

Reference yield:

: (R)-3-Amino-9-benzyloxy-nonanoic acid methyl ester

: 303007-77-4
(3S,4R,6R)-(4-hydroxy-6-(6-tert-butyldiphenylsiloxy)hexyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: methanol / 20 °C

2: 63 percent / NaHCO₃ / dioxane / 5 h / 30 °C

3: Na / benzene; methanol / 48 h / 20 °C

4: triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

5: H₂ / Pd/C / ethyl acetate / 24 h / 50 °C / 22801.5 Torr

6: H₂ / Raney-Ni / ethyl acetate; H₂O / 24 h / 80 °C / 60804.1 Torr

7: 3.9 g / TsOH / methanol / 1 h / 20 °C

8: 85 percent / triethylamine; DMAP / CH₂Cl₂ / 6 h / 20 °C

With dmap; hydrogen; sodium; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; nickel; In 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; benzene; 1: Michael addition / 2: Acylation / 3: Dieckman condensation / 4: Substitution / 5: Catalytic hydrogenation / 6: Catalytic hydrogenation / 7: Hydrolysis / 8: Substitution;
DOI:10.1021/jo000447q